4-Methoxybenzylamine → HCID 87191910, compound

HRID 2089020Notes

Reaction equation

HRID 2089020 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH2:36])=[CH:31][CH:30]=1>C(#N)C>[Cl:26][C:4]1[N:3]=[C:2]([NH:36][CH2:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 866498693-(2,6-dichloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 87191910HCID 87191910, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 7a (0.500 g, 1.24 mmol) and (4-methoxyphenyl)methanamine (1.018 g, 7.42 mmol) in acetonitrile (7 mL) was heated at 180° C. for 110 minutes The solvent was evaporated. The residue was treated with EtOAc and washed with 20% brine and 5% citric acid. The organic layer was concentrated and purified on a 100 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (98:2 to 95:5) to give 0.250 g of the title compound.

Workup

  1. customwas evaporated
  2. additionThe residue was treated with EtOAc
  3. washwashed with 20% brine and 5% citric acid
  4. concentrationThe organic layer was concentrated
  5. custompurified on a 100 g column
  6. washeluting with CH2Cl2/EtOAc (98:2 to 95:5)

Sources & evidence

ORD record
ord-dfa543197cdc4fbab9f7cb24bdd4dd30
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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